γ-Rhodomycinon | 17514-35-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 并四苯
• 英文名称: γ-Rhodomycinon
• 英文别名: γ-rhodomycinone；(9R,10R)-9-ethyl-4,6,9,10,11-pentahydroxy-8,10-dihydro-7H-tetracene-5,12-dione
• CAS: 17514-35-1
• 化学式: C₂₀H₁₈O₇
• 分子量: 370.359
• InChiKey: IYYYSIPRDYPSFJ-WOJBJXKFSA-N

物化性质

• 熔点：
  256 °C
• 沸点：
  623.1±55.0 °C(Predicted)
• 密度：
  1.602±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  27
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  135
• 氢给体数：
  5
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  γ-Rhodomycinon 生成 beta-紫红霉酮
  参考文献：
  名称：

  Krohn, Karsten; Hamann, Ingo, Liebigs Annalen der Chemie, 1988, p. 949 - 954

  摘要：

  DOI：
• 作为产物：
  描述：

  beta-紫红霉酮 生成 γ-Rhodomycinon
  参考文献：
  名称：

  Biedermann; Braeuniger, Pharmazie, 1972, vol. 27, # 12, p. 782 - 789

  摘要：

  DOI：

文献信息

• Regio- and stereo-selective construction of anthracyclinones: total synthesis of (–)-γ-rhodomycinone
  作者：Hiromichi Fujioka、Hirofumi Yamamoto、Hiroshi Kondo、Hirokazu Annoura、Yasuyuki Kita

  DOI：10.1039/c39890001509

  日期：——

  The first asymmetric synthesis of (–)-γ-rhodomycinone (1a) was achieved through a novel regioselective coupling reaction of the chiral AB-(2) and CD-building blocks (3).

  通过手性AB-（2）和CD-结构单元（3）的新型区域选择性偶联反应，实现了（-）-γ-鼠李糖酮（1a）的首次不对称合成。
• Asymmetric Synthesis of Anthracyclinones: Synthesis of a New Chiral AB-Synthon, (5R,6R)-6-Ethyl-5,6-dihydroxy-5,6,7,8-tetrahydro-1,4-naphthoquinone, and Its Application for a Novel Regioselective Synthesis of (-)-.GAMMA.-Rhodomycinone.
  作者：Hiromichi FUJIOKA、Hirofumi YAMAMOTO、Hirokazu ANNOURA、Hiroshi MAEDA、Yasuyuki KITA

  DOI：10.1248/cpb.40.32

  日期：——

  A new chiral AB-synthon, (5R, 6R)-6-ethyl-5, 6-dihydroxy-5, 6, 7, 8-tetrahydro-1, 4-naphthoquinone (4), for the synthesis of optically active rhodomycinones was prepared stereoselectively from a (-)-α-hydroxy ketone (6). The coupling reactions of 4 with homophthalic anhydride derivatives (9, 12) proceeded in a regioselective manner to give the tetracyclic compounds 10 and 13, respectively. Compound 10 was converted to (-)-γ-rhodomycinone (3) in a two-step sequence. The optical purity (100% ee) of 3 was unambiguously determined by high performance liquid chromatography analysis using a chiral column.

  一种新的手性AB-合成物（5R，6R）-6-乙基-5，6-二羟基-5，6，7，8-四氢-1，4-萘醌（4）用于合成具有光学活性的罗丹霉素，它是从（-）-α-羟基酮（6）中通过立体选择性制备的。4与邻苯二甲酸酐衍生物（9，12）的偶联反应以位点选择性方式进行，分别得到四环化合物10和13。化合物10通过两步反应转化为（-）-γ-罗丹霉素（3）。3的光学纯度（100% ee）通过手性柱高效液相色谱分析明确确定。
• Differentiation inducing activity of anthracycline compounds in friend leukemia cells.
  作者：Tomoko TSUJI、Hajimu MORIOKA、Misako TAKEZAWA、Toshihiko ANDO、Asao MURAI、Hiroshiro SHIBAI

  DOI：10.1271/bbb1961.50.1697

  日期：——

  Several kinds of anthracyclines having γ-rhodomycinone as the aglycone were isolated from Streptomyces cosmosus TMF 518, and their derivatives were prepared by chemical modification. We tested their differentiation inducing activity in Friend leukemia cells and clarified their structure activity relationship as follows: 1) The aglycone, γ-rhodomycinone, had no differentiation inducing activity but was cytotoxic; 2) the compounds with two sugar chains at both C7 and CIO had more potent differentiation inducing activity than those with only a sugar chain at C-10; 3) cosmomycin C was the most favorable candidate for an anticancer agent of all anthracyclines tested, because the value of ED50 (cytotoxicity)/ED50 (differentiation) was as high as 3000; and 4) the increase in differentiation inducing activity and cytotoxicity was not always in parallel.

  我们从宇宙链霉菌 TMF 518 中分离出几种以γ-罗多霉素酮为苷元的蒽环类化合物，并通过化学修饰制备了它们的衍生物。我们测试了它们在Friend白血病细胞中的分化诱导活性，并阐明了它们的结构活性关系如下：1）γ-罗多霉素酮没有分化诱导活性，但具有细胞毒性；2）C7 和 CIO 处有两条糖链的化合物比 C-10 处只有一条糖链的化合物具有更强的分化诱导活性；3）在所有测试的蒽环类化合物中，宇宙霉素 C 是最有利的抗癌候选药物，因为 ED50（细胞毒性）/ED50（分化）值高达 3000；以及 4）分化诱导活性和细胞毒性的增加并不总是同步的。
• Combined preparation comprising anthracycline derivatives
  申请人：Nerviano Medical Sciences S.r.l.

  公开号：EP1977753A1

  公开（公告）日：2008-10-08

  The present invention relates to combined preparations comprising a morpholinyl anthracycline administered in combination anticancer agents chosen from an alkylating agent, an antimetabolite, a topoisomerase I inhibitor and an antimitotic drug, which are useful for anticancer therapy, particularly in the treatment of a primary or metastatic liver cancer.

  本发明涉及由吗啉基蒽环类与选自烷化剂、抗代谢物、拓扑异构酶 I 抑制剂和抗有丝分裂药物的抗癌剂联合给药的组合制剂，该制剂可用于抗癌治疗，特别是治疗原发性或转移性肝癌。
• FUJIOKA, HIROMICHI;YAMAMOTO, HIROFUMI;KONDO, HIROSHI;ANNOURA, HIROKAZU;KI+, J. CHEM. SOC. CHEM. COMMUN.,(1989) N0, C. 1509-1511
  作者：FUJIOKA, HIROMICHI、YAMAMOTO, HIROFUMI、KONDO, HIROSHI、ANNOURA, HIROKAZU、KI+

  DOI：——

  日期：——